Thank you all for the responses.
ericrugiero: I think the idea of doing half and half or just easing in slowly makes the most sense and I could wait as I do until it is time for my income to cross the SS deduction limit to double my employee side of my contributions which occurs around June/July given my income (not that we live that way but I've now changed my paycheck contribution four times in the last four pay periods and if there's a human operator behind it, they're going to be wondering what's happening*). Thank you for the suggestion!
We make ~$300K+/year with a tax bracket of MFJ of 24% I think but I believe our effective tax rate last year was 27%.
PhrugalPhan: As I mentioned, I hope to work as long as I live/can. My wife is technically retired but is a serial entrepreneur and is always looking to do something to keep herself busy which generates some income sometimes. We both have smaller sources of income outside of the traditional salary (consulting, investments, etc.), included in the figure above. Yes to the inheritance (50% for charity, 50% for our offspring). The other two answers are below. As to where, currently NY. We're thinking of buying some property south (FL to TX) and we have a home outside the US (Thailand mostly, which is where I'd like to be at the end).
Vapour: Yeah, it is a good deal but an additional 6% is taken out of my salary and my employer matches 8% on top of the $19,500 voluntary contribution which is not matched. This 14% is considered "mandatory" contributions and is listed as a 414(h) pickup so it doesn't get counted as a voluntary employee contribution which is another 7% or so. I will reach 50 in a couple of years and plan to contribute the 6K or so more since right now I couldn't even contribute the full $19,500 before hitting the 57K limit*. The bottom line is that I contribute as much as possible of the $19,500 on top of what gets "picked up" by my employer to reach 57K. (I wonder even if I can contribute more via the 457 mechanism but I'm not sure, I think the $57K is the hard limit so far at least according to my accountant except for the $6000 I can contribute on behalf of my wife.)
And yes, I have a large Rollover IRA that can invest in a huge diversity of funds and that is about half my retirement portfolio. The other half is in the the 403(b) and the 414(h) pickup accounts which are separate. So three retirement accounts total, all at Fidelity. I was given the option to rollover what is in my IRA into the 403(b) when I switched employers but it didn't make sense since my new employer provides only a limited set of choices for investment whereas I wanted to keep the option open to a full fledged brokerage and it helps with fund diversification at least. Not sure if I still can do it but again, aside from limiting my investment choices, what difference would it make? It would still be a tax deferred and if I wanted to put it into the Roth portion, my tax bracket is high enough it'd be a big chunk of that. It seems contributing to the Roth 403(b) and then slowly rolling over portions as I get older may be the way
MDM: If I keep working, I expect my salary will keep rising. The only reason I can see myself stopping is for something I don't see right now. If it happens, then our income will be low and of course it makes sense to do the conversion then. But there's a risk it never happens UNLESS I die first in which case does my wife would likely be in the lowest bracket. I guess that's a way to look at it: likely as long as I'm alive, it'll be a higher income bracket at age 70 but unlikely otherwise (not certain either way---my wife has had some periods where she once made more than me before but she doesn't seem to want to work like that again).
If I could plan it out, i.e., I knew ahead of time when I was going to die, I could retire a year or two before my death and then get my income to the lowest bracket and then do the conversion. So at some advanced age, I could just do it or even take a leave of absence, we'll see.
--Ram
* this is a complicated story as to why but when you are trying to get as close to the the $57K limit as possible, and the contributions don't show up right away all of a sudden (never happened before) -- apparently they have the month it is deducted from my paycheck + 15 business days to do it - perhaps whoever they saw me coming close and ended up with manual checking so I don't go over but it seems to have gone in last night just fine on time (the previous three times it was delayed by as much as a month but varying wildy and varying between employee and employer contributions - weird).